Nanjo T,
*,
Oshita T,
Matsumoto A,
Takemoto Y.
*
Kyoto University, Japan
Late-Stage Installation of Dehydroamino Acid Motifs into Peptides Enabled by an N-Chloropeptide Strategy.
Chem. Eur. J. 2022;
28: e202201120
DOI:
10.1002/chem.202201120
Key words
dehydroamino acids - chlorination - azabicyclooctane - organocatalysis - late-stage modification
Significance
Late-stage modification of structural complex peptides bears enormous potential for drug discovery. The authors have developed a method for the formation and modification of dehydroamino acids.
Comment
The dehydroamino acids are prepared through N-chlorination of peptide bonds, with catalysis by 1-azabicyclo[2.2.2]octane (ABCO), and subsequent DABCO-induced b-elimination of an N-chloroamide. Various dehydroamino acids were obtained in moderate to excellent yields. The strategy permits the construction of a wide variety of dehydroamino acid residues in peptides and facilitates late-stage installation of such motifs into existing oligopeptides.
